What about a custom made pocket knife. I kinda agree that watches are becoming an antiquity. I don't see that many people with them anymore.
A knife will last a lifetime just like a watch and you can spend as much as you like.

My humble opinion, without reading through 3 pages of responses is, if you have to ask if something is appropriate, it most likely is not.

Okay, now that I have read through three pages of responses; I would never gift a watch unless I could afford a fairly expensive one. I wouldn't go as high as Rolex or Cartier, but perhaps a Citizen Eco-Drive, Bulova, Longines-Whitt​nauer or maybe Tag Heuer.

A pocket knife is great, until your next flight. Then it's some TSA agent's pocket knife.

Yes, indeed he just might be interested in pot, but anything over a couple of ounces would be tacky.

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For the last 3 years my son has been in boarding school. Finally it’s coming to the end in another month, give or take couple of days. Thru these 3 years he had one person, he is not a teacher, he kind of take care of boys including things like behavior, he is the one to go to if you need help finding a tutor, kind of in charge of many things. Us being outsiders it was not so easy for my kid to fit in at first and this guy really took care of him. Helped in every way possible.As the matter of fact he gets the credit for improve, well even restoring my son and ours (parents) relationship. My son kind of resisted us for a while for sending him away. He really helped. Anyways, I really would like to thank him at the end of the school for what he has done. Nothing too extravagant but I would like to buy something personal and memorable. Now for me it would be an engraved watch. Doesn’t have to be super fancy or anything. Say couple hundred dollars. Being that it is after school is done that I want to give him that, I hope it will not be considered like a bribe or anything. What do you think?

I would tell him that. If he lives close enough, I would invite him (and his wife, if he is married) to your home for cocktails or a homecooked meal with you and your family; & then I would express your thanks to him in person. If not, I would express it in a letter or card. Gifts and money-giving are not personal. People throw them in a drawer or spend the money. IMHO, your heartfelt appreciation & thanks is what people remember & treasure.

My humble opinion, without reading through 3 pages of responses is, if you have to ask if something is appropriate, it most likely is not.
...

First of all, I disagree with this statement. I am from a different country and what seems perfectly fine to you is totally foreign (no pan intended) to me and vice versa. What’s totally normal and even expected for me maybe inappropriate for you. By “you” I mean Americans, not you personally. Second of all, I do agree with the expensive watch thing. I would love to buy him a nice watch; he sure deserves it. Unfortunatelly I cannot afford one.

First of all, I disagree with this statement. I am from a different country and what seems perfectly fine to you is totally foreign (no pan intended) to me and vice versa. Whats totally normal and even expected for me maybe inappropriate for you. By you I mean Americans, not you personally.
Second of all, I do agree with the expensive watch thing. I would love to buy him a nice watch; he sure deserves it. Unfortunatelly I cannot afford one.

I would consider citizen Eco-drive fairly expensive (that's what mine is) and you can get a nice one for a few hundred. Solar powered with a life time warranty. Love my Eco drive!

I definitely agree with you, that an exemplary gift is the direction, however, a watch ... No. I would not. Why ? I would prefer to select my own watch or The Vet, Filippo would do the honors ...

However, here are some of my thoughts:

1) A Torah Scroll Door Amulet, that is made of silver, wood or brass or copper which is a talisman of Exemplary Luck for Jewish People ... I had forgotten its name, however, I had seen them on uncountable doors in Manhattan ... The symbolism is quite profound and it is a shared link or bond between you, your son and the Guidance Counsellor.

2) Another item which could be lovely is: A huge thick photographic coffee table book on: Traditional Jewish International Gastronomy or Sefardi Gastronomy of the Eastern Mediterranean.

3) A set of Dvd Travel - Food themed Documentries on Gastronomy in the Ancient Cities in the world of Judisim.

4) A 925 Sterling Silver or 18k Key chain with a symbol that connects Your Son and the Guidance Counsellor and You. He must open the door every day or every evening, and thus, he would remember and can be engraved.

1) A Torah Scroll Door Amulet, that is made of silver, wood or brass or copper which is a talisman of Exemplary Luck for Jewish People ... I had forgotten its name, however, I had seen them on uncountable doors in Manhattan

It's called a Mezuzah.

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If you love something, set it free. If it doesn't come back, HUNT IT DOWN AND KILL IT!